100572-72-3

Upstream product

• 100680-07-7 (2R,3R,4R)-3-Benzyloxy-1,2-O-isopropylidene-4-methyl-1,2,6-hexanetriol 
• 100-44-7 benzyl chloride 
• 100758-79-0 (2R,3R,4R)-3-Benzyloxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol 
• 88424-94-6 (1R,2R)-2-methyl-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 100680-08-8 (2R,3R,4R)-3-Benzyloxy-4-methyl-1,2,6-hexanetriol 

Downstream Products

• 100572-77-8 Methyl (2S,3S)-2-benzyloxy-5-hydroxy-3-methylpentanoate 
• 100572-76-7 (3R,4S)-4-Methyl-2-oxo-3-oxanyl benzoate 
• 100758-71-2 (3S,4S)-3-Benzyloxy-4-methyl-2-oxanone 
• 100758-72-3 (3R,4R)-3-Benzyloxy-4-methyl-2-oxanone 

Relevant academic research and scientific papers

Remarkably stable tetrahedral intermediates: Carbinols from nucleophilic additions to N-acylpyrroles

Sufficiently stable intermediates formed in the reaction of N-acylpyrroles (1) with hydride and Grignard reagents can undergo further synthetic transformations and chromatographic purification to enable the generation of pyrrolecarbinols 2 in 76-95% yields [Eq. (1)].

Stereocontrolled Synthesis of all Four Stereoisomers of Verrucarinolactone from (R)-2,3-O-isopropylideneglyceraldehyde

A practical synthesis of (+)- and (-)-verrucarinolactone (2) and epiverrucarinolactone (1) from (R)-2,3-O-isopropylideneglyceraldehyde via the key intermediates 3a/b is described.